Reaction Steps
Ethyl 1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate. The title compound was prepared by alkylation of ethyl 1H-pyrrolo[2,3-c]pyridine-5-carboxylate with 4-fluorobenzyl bromide in a manner similar to step (a) of example 1. 1H NMR (CD3OD) δ: 8.91 (s, 1H), 8.62 (s, 1H), 7.90 (d, 1H, J=3.0 Hz), 7.42 (m, 2H), 7.20 (m, 2H), 6.90 (d, 1H, J=3.0 Hz), 5.75 (s, 2H), 4.60 (q, 2H, J=7.0 Hz), 1.60 (t, 3H, J=7.0 Hz). LCMS (API-ES, M+H+): 299.1. (b) 1-(4-Fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid. The title compound was prepared by hydrolysis of ethyl 1-(4-fluoro-benzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate in a manner similar to step (b) of example 1. 1H NMR (DMSO-d6): δ: 8.97 (s, 1H), 8.35 (s, 1H), 7.90 (d, 1H, J=3.0 Hz), 7.35 (m, 2 H), 7.15 (m, 2H), 6.76 (d, 1H, J=3.0 Hz), 5.67 (s, 2H). LCMS (API-ES, M+H+): 271.1. (c) 1-(4-Fluorobenzyl)-N-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxamide. The title compound was prepared by coupling of 1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid with hydroxylamine hydrochloride in a manner similar to step (c) of example 1. 1H NMR (DMSO-d6) δ: 11.12 (s, 1H), 8.90 (s, 1H), 8.83 (s, 1H), 8.21 (s, 1H), 7.85 (d, 1H, J=3 Hz), 7.36 (d, 2H, J=8.3 Hz), 7.17 (d, 2H, J=8.4 Hz), 6.71 (d, 1H, J=3.0 Hz), 5.59 (s, 2H). LCMS (API-ES, M+H+): 286.1. HRMS calcd for C15H13FN3O2 (M+H) 286.0992, found 286.0978. Anal. (C15H12FN3O2) C, H, N. HPLC: 96.6% purity.
